Christopher Cross Financed His Breakthrough Selling Weed

Christopher Cross never had a rock star demeanor, but he burst onto the scene in the pre-MTV era when how you looked meant less than how you sounded. He’d score eight straight Top 40 hits between 1979-83 anyway, including two No. 1 singles.

Yet a new film called Yacht Rock: A Dockumentary reveals a surprisingly rough-hewn past. The guy who sang “Ride Like the Wind” used to be a drug dealer. In fact, Cross financed his five-times platinum Grammy-winning self-titled breakthrough through marijuana sales.

“The original demos I did, all the songs ended up on the record,” Cross says in the movie, which premiered earlier this month at the DOC NYC festival. “I financed my original songs by selling weed. I had a very successful weed business, and I bought a tape machine and some consoles and stuff and invested in a studio in Austin.”

READ MORE: The Night Christopher Cross Sat in With Deep Purple

It’s unclear what role smoking his own product played in a subsequent mishap, but Cross only got signed to Warner Bros. because he sent the resulting tapes to an incorrect address. The assistant who received the package instead liked Cross’ work so much that he forced his boss, the legendary music industry executive Lenny Waronker, to have a listen.

“Lenny told me years later that had I just sent it to A&R, it would have been rejected outright,” Cross says, “because they weren’t really accepting anything. So it was pretty serendipitous that I sent it to the wrong guy.”

Christopher Cross would reel off four debut hit singles at the turn of the ’80s – No. 2 “Ride Like the Wind,” No. 1 “Sailing,” No. 15 “Never Be the Same” and No. 20 “Say You’ll Be Mine” – while winning a total of five Grammys, including Album of the Year.

Listen to Christopher Cross’ ‘Ride Like the Wind’

An Acid Trip Led to Christopher Cross’ First Hit

“Ride Like the Wind,” one of the songs that cemented Cross’ place in the yacht rock genre, had its own drug-fueled beginnings amid live jams while covering of Paul McCartney and Wings‘ “Nineteen Hundred and Eighty Five” from Band on the Run.

“I was playing at a club in Houston,” Cross says, “and in the middle of that song, I started doing this [mimics the hook of ‘Ride Like the Wind’] and people would go crazy. They started dancing and moving around. It just seemed to really connect with the audience, so we would just jam on that riff.”

The song came together as they returned to Austin to record. “I was sitting in the front seat of the van and had taken acid,” Cross added, “and I wrote the words to ‘Ride Like the Wind,’ driving from Houston to Austin, on acid.”

Yacht Rock: A Dockumentary debuts Nov. 29 on HBO and will also stream on Max.